Flour compositions and baked products with sodium, potassium and calcium salts of n-alkanoylglycines and alanines included therein



United States Patent 3,365,300 FLOUR COMPOSITIONS AND BAKED PRODUCTSWITH SODIUM, POTASSIUM AND CALCIUM SALTS 0F N-ALKANOYLGLYCINES AND ALA-NINES INCLUDED THEREIN Paul D. Thomas, Groton, Conm, assignor to Chas.Pfizer 8: Co., New York, N.Y., a corporation of Delaware No Drawing.Filed Jan. 13, 1965, Ser. No. 425,345 6 Claims. (Cl. 99-91) ABSTRACT OFTHE DISCLOSURE Sodium, potassium and calcium salts of N-alkanoylglycinesand'alanines containing from 14 to 20 carbon atoms in the alkanoylgroup, incorporated in a farinaceous composition in an amount of atleast 0.1%, based on the Weight of flour employed in composition.

The invention described in this application relates to certain novelflour or 'farinaceous compositionsyMore particularly, it is concernedwith various N-acyl amino acid derivatives which have been found to beof value in the food industry when used in conjunction with flour. Theinvention includes the use of these compounds as well as the flourcompositions containing them within its scope.

In the baking art, natural variations in flour characteristics have beenthe source of a continuous problem or obstacle to the workers in thisfield even when flours of the highest quality grade are carefullyselected. Long a problem in conventional baking, this matter has nowbeen further accentuated in continuous bread processing. In accordancewith the present invention, on the other hand, the compounds disclosedand used herein help to even out variations in flour characteristics inview of the marked dough strengthening properties which they exhibit. Asa result, greater tolerances are now provided in the mixing, fermentingand machining operations, causing a baked product to be obtained withimproved grain and texture as well as over-all quality. In addition, therate of crumb firming is retarded and there is also no need to-use suchstarch emulsifiers as mono-diglycerides and calcium stearyl-2-lactylate,etc.

The compounds which are included within the purview of this inventionare all selected from the class consisting of N-acyl amino acid salts ofthe formulae:

wherein R is a member selected from the group consisting of hydrogen andmethyl, M is a metallic cation selected from the group consisting ofsodium, potassium and calcium, and R is an alkyl radical of fromthirteen to nineteen carbon atoms. Typical member compounds of thisseries include sodium N-stearoyl-DL-a-alanine, sodium N stearoyl Balanine, sodium N palmitoyl DL a alanine, potassium N palmitoyl [3alanine, calcium N myristoyl DL u alanine, calcium N- arachidoyl DL ualanine, sodium N stearoylglycine, sodium N-palmitoylglycine, and so on.All these compounds are useful as bread softening agents in view oftheir ability to retard the firming, i.e., the staling rate, of breadwhen incorporated into the dough of the baking mix prior to baking.

The process employed for preparing the useful compounds of thisinvention involves first treating the appropriate amino acid startingmaterial with the desired higher alkanoyl halide of choice in accordancewith conventional organic procedure, and then subsequently convertingthe N-alkanoyl amino acid so formed to the corresponding alkali metal orcalcium salt thereof with either sodium, potassium or calcium hydroxide,as the case may be. Actually, many of the N-alkanoyl amino acidintermediates of this invention are known compounds and have alreadybeen reported in the literature. For instance, N-palmitoylalanine hasbeen prepared by M. Naudet (Bull. Soc. Chim., France, 1950, pp. 358-361)starting from alanine and palmitoyl chloride, and using aqueous sodiumhydroxide as the reaction medium therefor. However, the utility reportedtherein for such a compound was that of a good detergent agent and notthat of a bread softening agent. Additionally, Fieser et al., in theJournal of the American Chemical Society, vol. 78, p. 2825 (1956),report on the preparation of N-stearoyl-DL-a' alanine by a differentmethod, starting from alanine ethyl ester hydrochloride and proceedingto the ethyl ester of N-stearoyl-DL-u-alanine via stearic acid in thepresence of triethylamine and isobutyl chlorocarbonate.

In connection with a more detailed consideration of the preferred methodof synthesis for these compounds, i.e., the N-alkanoyl amino acid saltshaving the aforementioned bread softening properties, the correspondingN- alkanoylglycine or alanine having from 14 to 20 carbon atoms in thealkanoyl group is contacted with either sodium, potassium or calciumhydroxide, as the case may be, in accordance with conventional procedurein an aqueous organic solvent system. In practice, it is preferable toemploy an aqueous alcoholic or aqueous acetone solutions of theN-alkanoyl amino acid compound containing an equivalent amount in molesof the appropriate metal hydroxide. The desired salt soon precipitatesfrom solution almost immediately upon completion of this step. Othersolvents which may be used here in place of acetone include other loweralkyl ketones such as methyl ethyl ketone, diethyl ketone, methylisoamyl ketone, and the like, while suitable alcohol solvents includesuch lower alkanols as methanol, ethanol, isopropanol, tertiary-butanol, and so on. The calcium N-alkanoyl glycines and alanines ofthis invention may, alternatively, also be prepared from thecorresponding monoalkali compounds thus formed, by means of a simplemetathetical reaction involving the use of a calcium halide salt, suchas calcium chloride or bromide, in an aqueous system to afford thedesired calcium compound useful as a bread softener.

As previously indicated, the compounds of this invention are all usefulas bread softening agents to prevent staling, in addition to beinguseful for improving the con dition of the dough as Well. In carryingout the baking process proper, only minor proportionate amounts of theinstantly claimed compounds need be used in the dough batch or bakingmix in order to achieve effective results in this connection. Forinstance, concentrations as low as 0.1% by Weight of the compound, basedon the Weight of the flour, have been found to be effective and, ingeneral, One need only employ these compounds at levels that are in therange of from about 0.1% up to about 3% by Weight of the softening agentin order for highly satisfactory results to be achieved. Moreover, thesodium, potassium and calcium salts of the N-alkanoyl amino acids ofthis invention accomplish their useful firmnessretarding activity inbread without causing any adverse side effects to occur, i.e., they donot adversely affect the crumb size, grain, crust, color, texture,specific volume of flavor of the finished bread products when the latterare baked under normal, standard conditions. The breadsoftening activityof these compounds is also surprising when one considers that thecorresponding N-alkanoyl amino acids from which they are derived lackthis activity to a substantial degree.

Additionally, the compounds of this invention impart improved qualitiesin general, including anti-staling properties, to such baked products asrolls, doughnuts, biscuits, cakes, pastries and the like, as well asbread, when added to the dough in the quantities previously indicated.For instance, among the specific advantages which have been realized bytheir use in this manner with respect to the yeast-leavened productsare: (1) retardation of crumb firming; (2) improved dough handlingcharacteristics; (3) improved ingredient and processing tolerances; (4)reduction in proof time; and (5) improved physical characteristics, suchas the grain, texture and volume of the finished baked goods.Furthermore, chemicallyleavened baked products also benefit equally aswell by the use of these compounds in the baking dough or batter priorto baking in the same manner as before. Thus, for example, improvedbatter and/ or dough handling characteristics have resulted, as well asimproved finished goods properties and firmness development with respectto the crumb quality. In almost every case, the most outstandingcompound of all those tested and the one which is, therefore, the mostpreferred member of this invention is sodium N-stearoyl-DL-ot-alanine.

Moreover, the compounds of the present invention are useful infarinaceous starch products in the food field in general. For instance,they have been found to impart improved properties to the quality andtexture of such products as grain cereals, macaroni and the like, ifsaid products are first treated with these compounds just prior tocooking. The advantages altorded by the use of these compounds in thismanner, i;e., as applied to starch-based foods, are manifold: forinstance, they prevent undesirable stickiness and pastiness fromoccurring in said products, thereby resulting in increased productionadvan tages as well as in increased consumer appeal of the finishedproduct. Examples of practical illustrations of the present inventioninclude the use of these compounds in such starch-based foods as instantpotato flakes or granules, macaroni products and spaghetti, hotbreakfast food cereals, and the like, and starch-based piefillings anddessert puddings, as well as in dehydrated creamed soups and variousrice products, etc. In each case, the starch-containing product isimproved as to both its quality and texture in view of the ability ofthese compounds to reduce the inherent stickiness and pastiness of thestarch-containing food material as previously indicated.

In accordance with the process of this invention for effecting saidimprovement in starch-based foods, a starch-containing or starch-basedfood material is first treated with a relatively minor amount of theorganic compound heretofore mentioned just prior to the cooking step. Ingeneral, all that is usually necessary is to use at least about 0.1% byweight of the compound based on the total weight of the starch-basedfood material. In some instances, even less than this amount may beeffective, but it is generally not advisable to go below theaforementioned lower limit. The upper limit can be preferably set atabout 3% although this is not really critical and amounts as high as 5%by weight have been used. Nevertheless, there is no real appreciableadvantage to be gained in exceeding the aforementioned 3% weight limit.The important point to remember is that the addition and subsequentmixing steps must be accomplished prior to the cooking of thestarch-based food material. Of especial interest in this connection isthe fact that sodium N-stearoyl-DL-a-alanine is particularly valuable asan agent for improving the quality and texture of macaroni products. Forinstance, this compound is reported to increase the firmness of the foodproduct itself, as well as to improve its tolerance to overcooking andto prevent clinging and stickiness of the individual noodle strands fromoccurring. These improved properties of the finished food material areof especial value in those cases where the macaroni product is intendedfor use in the canning industries and in the institutional trades, suchas in mass feeding establishments, etc.

In summary, therefore, the present invention is concerned withfarinaceous compositions comprising flour and at least about 0.1% byweight based on said flour of a compound selected from the groupconsisting of the sodium, potassium and calcium salts of N-alkanoylglycines and alanines containing from 14 to 20 carbon atoms in thealkanoyl group. More particularly, it is concerned with farinaceouscompositions comprising the flour and from between about 0.1 to about 3%by weight based on said flour of a compound of the type as hereinbeforedescribed. The preferred compounds for these food compositions are theN-alkanoylalanines of from 16 to 18 carbon atoms in the alkanoyl groupand especially, sodium N-stearoyl-DL-a-alanine, sodium N-stearoyl-,B-alanine and sodium N-palmitoyl-DL-a-alanine. The flour present inthese compositions can preferably be a wheat flour of either thebleached or unbleached variety and it is normally present in intimateadmixture with the compound of choice. Needless to say, the bakedleavened dough products so produced from these compositions also liewithin the scope of this invention, as do aqueous farinaceouscompositons containing these compounds at the aforementioned weightlevels.

Moreover, the invention also includes within its scope the method ofimproving the properties of aqueous farinaceous dispersions, whichcomprises the step of incorporating therein at least about 0.1% byweight, based on the weight of the flour, of the compound heretoforementioned, i.e., one selected from the group consisting of the sodium,potassium and calcium salts of N- alkanoyl glycines and alaninescontaining from 14 to 20 carbon atoms in the alkanoyl group. Moreparticularly, it is concerned with the method of retarding the stalingrate of various baked leavened dough products. This is accomplished byincorporating the compounds of the present invention in saidcompositions at concentration levels ranging from between about 0.1 toabout 3% by weight, based on the weight of the flour contained in saiddough. As previously indicated, the preferred compounds for these ediblestarch compositions are the N- alkanoylalanine salts containing from 16to 18 carbon atoms in the alkanoyl group.

This invention is further illustrated by the following examples, whichare not to be construed in any way or manner as imposing limitationsupon the scope thereof. On the contrary, it is to be clearly understoodthat resort may be had to various other embodiments, modifications andequivalents thereof which readily suggest themselves to those skilled inthe art without departing from the spirit of the present inventionand/or the scope of the appended claims.

EXAMPLE I In a 2-liter, four-necked flask fitted with stirrer,thermometer, dropping funnel, nitrogen-inlet tube and reflux condenserhaving drying tube attached at the top, there were placed 180 g. (2.0moles) of DL-a-alanine suspended in 500 ml. of 1,2-dimethoxyethane. Theresulting slurry was then heated under a nitrogen atmosphere to refluxtemperatures (86 C.), while 303 g. (1.0 mole) of stearoyl chloride wasadded to the mixture from the dropping funnel over a twenty-minuteperiod. At the end of this time, the reaction mixture was refluxed forseven hours and then subjected to vacuum distillation to remove thesolvent. The residual material was then taken up in 1000 ml. of warmchloroform and washed with three-200 ml. portions of cold water. Uponevaporation of the washed chloroform layer to dryness while underreduced pressure, there was obtained 355 g. of a yellow oil which soonsolidified to a cream-colored solid on standing. This amounted to a 47%yield of N-stearoyl-DL-tx-alanine, M.P. 114117 C.

Analysis.Calcd. for C H NO: acid value, 158. Found: acid value, 155.

EXAMPLE H The procedure described in Example I is repeated exactly toprepare N-stearoyl-B-alanine by merely substituting the same amount offl-alanine in place of DL-a-alanine as starting material for thisreaction.

In like manner, the use of glycine on an equivalent weight basis inplace of DL-u-alanine in this same reaction affords N-stearoylglycine asthe desired product.

EXAMPLE III The procedure described in Example I is followed to prepareN-palmitoyl-DL-u-alanine starting from this amino acid, but usingpalmitoyl chloride in place of stearoyl chloride on an equivalent Weightbasis.

EXAMPLE IV The procedure described in Example I is followed to preparethe following N-acyl amino acid compounds, starting from the appropriatemolar amounts of amino acid and corresponding acyl chloride reagent ineach case:

N-palmitoyl-B-alanine N-palmitoylglycine N-myristoyl-DL-a-alanineN-myristoyl-,B-alanine N-myristoylglycine N-arachidoyl-DL-a-alanineN-arachidoyl-fi-alanine N-arachidoylglycine EXAMPLE V EXAMPLE VI Theprocedure described in Example V is followed to prepare other sodiumsalts, viz., the salts of those acids previously reported in ExamplesII-IV. In each and every case, equimolar quantities of reactant andreagent are employed as in Example V. In this manner, the followingcompounds are obtained:

sodium N-stearoyl-B-alanine sodium N-stearoylglycine sodiumN-palmitoyl-DL-a-alanine sodium N-palmitoyl-fl-alanine sodiumN-palmitoylglycine sodium N-myristoyl-DL-a-alanine sodium N-myristoyl-flalanine sodium N-myristoylglycine sodium N-arachidoyl-DL-tx-alaninesodium N-arachidoyl-fi-alanine sodium N-arachidoylglycine EXAMPLE VIIThe procedure described in Example V is followed to prepare thepotassium salts of the acids previously reported in Examples I-IV. Thisis accomplished by employing potassium hydroxide in place of sodiumhydroxide on an equivalent molar basis in this reaction. The compoundsobtained in this manner are listed below as follows:

potassium N-stearoyl-DL-ot-alanine potassium N-stearoyl-B-alaninepotassium N-stearoylglycine potassium N-palmitoyl-DL-a-alanine potassiumN-palmitoyLB-alanine potassium N-palmitoylglycine potassiumN-myristoyl-fi-alanine potassium N-myristoyl-B-alanine potassiumN-myristoylglycine potassium N-arachidoyl-DL-a-alanine potassiumN-arachidoyl-B-alanine potassium N-arachidoylglycine EXAMPLE VIII Theprocedure described in Example V is followed to prepare the calciumsalts of the acids previously reported in Examples I-IV. This isaccomplished by employing calcium hydroxide in place of sodium hydroxideon an equivalent molar basis in this reaction. The compounds obtained inthis manner are listed below as follows:

calcium N-stearoyl-DL-a-alanine calcium N-stea'royl-B-alanine calciumN-stearoylglycine calcium N-palmitopl-DL-a-alanine calciumN-pahnitoyl-B-alanine calcium N-palmitoylglycine calciumN-myristoyl-DL-a-alanine calcium N-myristoyl-fl-alanine calciumN-myristoylglycine calcium N-arachidoyl-DL-a-alanine calciumN-arachidoyl-B-alanine calcium N-arachidoylglycine EXAMPLE IX SodiumN-stear-oyl-DL-u-alanine, prepared as described in Example V, wasincorporated into a bread recipe having the following formula:

4-hour sponge Grams Flour 1120 Water 615 Yeast 4O Dough conditioner 1 8Potassium. bromate, 0.3%; ammonium chloride, 9.7%;

gtglg ium sulfate, 25%; sodium chloride, 10%; and starch,

Dough portion Grams Flour 480 Water 417 Sugar (granulated) 128 Salt 34Calcium propionate 6 Milk powder 48 Lard 40 SodiumN-stearoyl-DL-a-alanine 8 The ingredients of the sponge [recipe areadded to the McDufiee bowl of a Hobart mixer in the order listed. Theingredients are mixed for one minute using the No. 1 speed. The bowl isthen scraped down and the sponge is again mixed for one minute at theN0. 2 speed. The sponge is removed from the bowl at this point andtransferred to a polyethylene bag and allowed to ferment at roomtemperature (-25 C.) for four hours.

A sponge separately prepared as described in the above section is thenplaced in a ten quart stainless-steel Hobart mixing bowl and the balanceof the ingredients are added as outlined under the dough portion of thebread recipe. The mixture is mixed on No. 1 speed for eight minutes. Theresultant dough is then removed from the bowl and placed in apolyethylene bag and allowed to ferment for 24 minutes at roomtemperature (-25 C.). It is then scaled into 1 lb. portions, with atleast four 11b. balls of dough being prepared for the subsequenttesting. The halls are rounded (rolled into small balls by hand in orderto exclude large air bubbles and gas pockets), and each ball is then runthrough the molder twice using a 7 inch setting for the first pass and Asetting for the second. The molded dough is rolled into a cylinderapproximately as long as the pan in which it is baked. The cylinder istightened by placing in the automatic rollers to fit bread pan lengthbetween the ends. It is then dropped into greased bread pans,transferred to the proof box and proofed for one hour at 120 F. and 55%relative humidity. The proofed dough is baked at 430 F. for 25 minutesand the resulting bread allowed to cool for one hour. This breadcontained the sodium N-stearoyl-DL-a-alanine additive at the 0.270%concentration level, based on the total weight of the dough, whichamounted to roughly 0.5% based on the flour. Three of the four breadloaves obtained are then packaged into polyethylene bags, and thesepackaged loaves are stored at room temperature and the compression datadetermined thereon at the end of 3, 4 and days of storage time,respectively. Each of the unpackaged loaves, on the other hand, issliced and compression data determinations are performed immediatelythereon so as to provide initial data readings.

The compression determinations on each loaf are conducted on two-l inchthick slices of bread, one slice being taken from the center of thebread and the other approxirnately one inch from the end. Thecompression test is performed with a standard penetrometer using al-ineh diameter flat stainless-steel disc in place of the usual vaselinecone. A 150 g. weight is used as the load on the end of the compressiondisc. The load is placed on the slice for a period of five seconds,after which time the penetration is determined in millimeters. Threecompressions are performed on each slice of bread, two in the bottomcorners of the slice and the third at the top center. All data isrecorded and the six values for each loaf are averaged. The resultsobtained in this manner at the concentration level tested (based onfiour weight) are presented below in the following table, which alsoincludes corresponding information on the monodiglyceride additive ofcommerce (Atmul 500), as well as a negative control (where there is anadditive persent) for comparison purposes:

Compression Data (mm.) Additive Initial 3 days 4 days 5 days None(control) 189 50 38 29 Monodiglyceride 1 182 70 60 NaN-stearoyl-DL-a-alanine. I89 88 69 57 Compression Data (mm. AdditiveInitial 3 days 4 days 6 days None (control) 189 50 38 Monodiglyceride182 70 30 Na N-stearoyl-Balanine 184 59 28 As in the previous example,it can be seen that the instant softening agent of choice is superior tothe control. Further, sodium N-stearoyl-p-alanine was also found to beequally as good as the monodiglyceride of commerce.

EXAMPLE XI The procedure described in Example IX is followed employingin place of sodium N-stearoyl-DL-a-alani'ne as the softening agent ofchoice any one of the other products reported previously in ExamplesVIVIII. In each and every case, the results obtained are substantiallythe same as those reported previously in the preceding two examples forsodium N-stearoyl-DL-ot-alanine and sodium N-stearoyl-fl-alanine,respectively.

Additionally, this same procedure is also repeated using the compoundsof choice at different concentration levels other than that previouslyreported on, i.e., 0.5 For instance, when sodium N-stearoyl-DL-u-alanineis employed at the 0.1% concentration level, based on the weight of theflour, the results obtained are substantially the same as thosepreviously indicated. In like manher, the use of 3.0% sodiumN-palmitoylglycine also affords similar results.

EXAMPLE XII The procedure described in Example IX was repeated asregards the preparation of the conventional sponge and doughformulation, including the added sodium N- stearoyl-DL-ot-alanine at the0.5% concentration level, based on flour weight. However, in thisparticular case, the dough improver eifects of the aforementionedalanine compound were investigated and breads were prepared using theoptimum mixing time of 3% minutes, as well as severe overmix conditionsof 7.5 minutes. Observations were then made on dough quality and on thequality of the finished goods, employing a negative control forcomparison purposes. In these tests, three loaves of bread were bakedfor each test sample or control at a given mixing time for the dough(dough mixing time or DMT, in minutes), and the results obtained werethereafter averaged. The following table summarizes the representativedata so obtained under these conditions, using a good quality breadflour /3 Montana, /3 Kansas Spring-65% absorption) for all the bakingstudies reported below:

DMT Loaf Loaf Sp. Vol., Additive (min.) Wght. Vol. cc./gn1. BreadAppearance and Dough Eflects None (control) 3. 25 398 2, 260 5. 68 Faircrumb and good color.

Na N-stearoyl-DL-a-alaninm 3. 25 398 2, 320 5. 83 Good crumb and goodcolor.

None (control) 7. 5 405 2, 090 5. 16 Poor crumb and fair color; dough v.

sticky and runny at makeup.

Na N-stearoyl-a-aianine 7.5 401 2,190 5. 46 Fair silky crumb and goodcolor; not

sticky and runny at makeup.

EXAMPLE X The procedure described in Example IX was followed here exceptthat sodium N-stearoyl-B-alanine, prepared as described in Example VI,was now employed as the softening agent of choice in place of sodiumN-stearoyl- DL-a-alanine at the same concentration level as used in theprevious experiment. The results obtained in this manner are summarizedbelow in the following table, which also includes the same control dataas in Example lX for comparison purpose;

From the above table, it is obvious that sodium N-stearoyl-DL-a-a'lanine is consistently superior to the negative control,Where there is no additive present, as regards both the grain andover-all bread quality. Further, the dough produced on overmixing in thecase of the instant N-stearoyl alanine composition is stronger andsubstantially less sticky and runny in appearance on make-up.

EXAMPLE XIII The procedure described in Example XII was followed exceptthat this time sodium N-stearoyl-B-a'lanine was 3,365,300 9 used inplace of the corresponding a-isomer on the same weight basis as before.The results obtained in this manner are summarized below in thefollowing table:

concentration levels, based on flour weight. The sodiumN-set-aroyl-DL-m-alanine is dry-blended with the cake flour at the startof the procedure in each instance. The

DMI Loaf Loaf Sp. Vol., Additive (min) Wght. Vol. cc./gm. BreadAppearance and Dough Effects None (control) 3. 398 2, 260 5. 68 Faircrumb and good color.

Na N-stearoylfl-alanine 3. 25 399 2, 260 5.66 Good crumb and good color.

None (control) 7. 5 405 2, 090 5. 16 Poor crumb and fair color; dough v.

sticky and runny.

Na N-stearoyLfl-alanine 7. 5 401 2,140 5. 34 Fair silky crumb and color;not stickv and runny at makeup.

EXAMPLE XIV The procedure described in Example XII is repeated againusing the other N-acyl amino acid salts reported previously in ExamplesVI-VIII. In each and every case, the results obtained showed that theother compounds of this invention work substantially as well as doughimproving agents when used in this manner as compared to theaforementioned sodium N-stearoylalanines.

Additionally, the same procedure is also repeated using the compounds ofchoice at different concentration levels other than that previouslyemployed. For instance, when sodium N-stearoyl-DL-a-alanine is employedat the 0.1% concentration level, based on the weight of the flour, theresults obtained are substantially the same as those previouslyreported. In like manner, the use of 3.0% sodium N palmitoyl-,8-alaninealso affords similar results.

EXAMPLE XV A high-sugar White cake is prepared in the following mannerfrom the ingredients listed below:

results obtained show that the treated cake samples, as in the case ofbread, are consistently superior to the nega tive control, as regardsboth the firmness retarding effect and the dough improver qualities aswell.

What is claimed is:

1. A composition of matter comprising flour in intimate admixture withat least about 0.1% by Weight based on the weight of said flour of acompound selected from the group consisting of the sodium, potassium andcalcium salts of N-alkanoylglycines and alanines containing from 14 to20 carbon atoms in the alkanoyl group.

2. A composition as claimed in claim 1 wherein the amount of compoundpresent in the mixture is from between about 0.1% up to about 3% byWeight based on the weight of said flour.

3. The composition of claim 1 wherein said compound is sodiumN-stearoylalanine.

4. The composition of claim 1 wherein said compound is sodiumN-palmitoylalanine.

Grams 5. An aqueous farinaceous dispersion having included Cake flour219 therein at least about 0.1% by weight based on the weight 2 53;--(;;I;; 3 of the farinaceous ingredient, of a compound selected Salt 7from the group consisting of the sodium, potassium and Milk solids(non-fat) 15 6 Calcium Salts of oy g ycines and alanines contain- COVQ Z100 mg from 14 to 20 C bon atoms in the alkanoyl group Egg whites 113 Abaked leavened dough product having i h Water 202 Standard baking powderis used here, i. e., of the double action variety comprising cornstarch, sodium bicarbonate, calcium acid phosphate and sodium aluminumsulfate.

2 Cove is the registered trademark name of the Procter & Gamble Co, fora plastic all-purpose vegetable shortening agent.

The first five ingredients in the above list are blended together forthree minutes at the No. 1 speed in a Hobart Kitchenaid mixer. This isthen followed by the addltion of the shortening, egg Whites and water tothe mix in one batch followed by the agitation of the whole at No. 2

therein from about 0.1% up to about 3% by weight, based on the Weight ofthe flour contained in said dough, of a compound selected from the groupconsisting of the sodium, potassium and calcium salts ofN-alkanoylglycines and alanines containing from 14 to 20 carbon atoms inthe alkanoyl group.

References Cited UNITED STATES PATENTS speed for 1.5 minutes, stoppingonly after each half-min- 31114O9 11/1963 Jackson at 99 91 ute to scrapedown the bowl. The batter is then checked for specific gravity and 425grams of same is then scaled FOREIGN PATENTS into an 8-inch roirnd cakepan. The baking is done at 652,006 4/1951 Great Britain.

375 F. for twenty-six minutes.

This entire procedure is then repeated again using sodiumN-stear-oyl-DL-a-alanine at both the 0.5% and 1% RAYMOND N. JONES,Primary Examiner.

